Unusual biomimetic oxidations of indoles: Synthesis of suaveoline and an alkaloid G analogue

Patrick D. Bailey, Keith M. Morgan, Georgina M. Rosair, Rhodri L. Thomas

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The one-pot conversion of ajmaline 1 into the nitrile 4 (X-ray structure) and suaveoline 2a is reported; both reactions utilise hydroxylamine hydrochloride in a refluxing alcohol, and involve unusual multi-step mechanisms in which the product ratio can be controlled by the choice of the alcohol. In an additional unusual oxidation, the synthetic intermediate 14 used in a synthesis of suaveoline can be oxidatively cyclized to 16.

Original languageEnglish
Pages (from-to)8255-8259
Number of pages5
JournalTetrahedron Letters
Volume40
Issue number47
DOIs
Publication statusPublished - 19 Nov 1999

Keywords

  • Alkaloids
  • Indoles
  • Oxidation

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